He Did It His Way: All the (Many) Women in Frank Sinatra’s Life

We can say a lot of thing about Ole’ Blue Eyes, like how he’s the original “swinger,” the world’s greatest crooner, an Oscar-winning actor, a drinker, a manic/depressive, an insomniac, and the leader of the Rat Pack. Oh, and let’s not forget: a ladies’ man. Frank Sinatra certainly loved women, and they certainly loved him. And what wasn’t to love? He was good-looking, charming, talented, and had the voice of a god.

A portrait of a woman / Frank Sinatra talking to a blonde woman with short hair / Frank Sinatra posing with a hat on / Frank Sinatra posing with a woman on the red carpet / A woman with short black hair

Photo by Vittoriano Rastelli, Corbis, Getty Images / Bettmann, Getty Images / Michael Ochs Archives, Getty Images / Bettmann, Getty Images / Sunset Boulevard, Corbis, Getty Images

According to Sinatra’s friend Joey D’Orazio, the crooner once confided to him: “I just want to make it with as many women as I can.” One of his go-to phrases, when he hung out with his pals in the lounge of the Sands hotel in Las Vegas, was, “We’re all men sitting there. Where are the broads?” Well, that sums it up! And let us sum it up even further while providing the full list of Sinatra’s ladies…